Cefdinir - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Transporters (3)

Targets (3)Transporters (3)Biointeractions (6)

Identification

Name

Cefdinir

Accession Number

DB00535 (APRD00644)

Type

Small Molecule

Groups

Approved

Description

Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. It was approved by the U.S. Food and Drug Administration (FDA) in December of 1997.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Cefdinir

Cefdinirum

CFDN

External IDs

BMY-28488 / CI 983 / CI-983 / FK 482 / FK-482

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Cefdinir monohydrate	6E7SN358SE	213978-34-8	QWUVJQSNISEEQI-KYIYMPJCSA-N	Details

Product Images

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cefdinir	Capsule	300 mg/1	Oral	Red Pharm Drug, Inc.	2008-01-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Teva	2007-05-09	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Rebel Distributors	2011-01-14	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Aurobindo Pharma	2007-12-14	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Rebel Distributors	2008-01-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2014-07-04	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Physicians Total Care, Inc.	2007-05-08	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2008-01-07	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2008-01-07	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A S Medication Solutions	2007-05-08	2017-06-20	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Preferreed Pharmaceuticals Inc.	2016-12-06	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Rebel Distributors	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Citron Pharma LLC	2008-01-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Aurobindo Pharma	2008-01-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2016-08-23	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2014-07-04	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Nucare Pharmaceuticals, Inc.	2014-07-04	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2015-08-20	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2014-05-01	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2014-05-01	2017-06-20	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Proficient Rx LP	2007-12-14	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Sandoz	2007-04-06	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Northwind Pharmaceuticals	2014-09-17	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	DAVA Pharmaceuticals, Inc.	2014-05-01	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	North Star Rx Llc	2007-12-14	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2007-05-01	2017-06-20	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Dispensing Solutions, Inc.	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Remedy Repack	2016-01-18	2017-01-12	US
Cefdinir	Capsule	300 mg/1	Oral	Red Pharm Drug, Inc.	2007-04-06	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Nucare Pharmaceuticals, Inc.	2007-05-08	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Nu Care Pharmaceauticals,inc.	2013-10-04	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2007-05-09	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2007-05-09	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Red Pharm Drug, Inc.	2014-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Sandoz	2007-04-06	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2007-05-01	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Aurobindo Pharma	2007-12-14	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Rebel Distributors	2007-12-14	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Proficient Rx LP	2007-05-08	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Physicians Total Care, Inc.	2007-05-09	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Teva	2007-05-08	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2008-01-07	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Red Pharm Drug, Inc.	2014-07-04	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Clinical Solutions Wholsesale	2007-12-14	2017-06-24	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A S Medication Solutions	2014-05-01	2017-06-20	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2008-01-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Blenheim Pharmacal, Inc.	2013-11-15	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	H.J. Harkins Company	2008-08-23	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	DAVA Pharmaceuticals, Inc.	2014-05-01	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	North Star Rx Llc	2007-12-14	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Physicians Total Care, Inc.	2007-05-08	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Avera Mc Kennan Hospital	2015-02-27	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A S Medication Solutions	2007-12-14	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Atlantic Biologicals Corps.	2014-02-07	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Avera Mc Kennan Hospital	2016-05-19	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Teva	2007-05-08	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A S Medication Solutions	2007-12-14	2017-06-20	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Aidarex Pharmaceuticals LLC	2007-12-14	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2008-01-07	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	A S Medication Solutions	2008-01-07	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Blue Point Laboratories	2014-02-07	Not applicable	US
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Sandoz	2007-04-06	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Northwind Pharmaceuticals	2015-02-10	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	DAVA Pharmaceuticals, Inc.	2014-05-01	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Aidarex Pharmaceuticals LLC	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Orchid Pharma Inc	2014-07-04	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2011-01-14	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	North Star Rx Llc	2008-01-07	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A S Medication Solutions	2007-05-01	2017-06-20	US
Cefdinir	Capsule	300 mg/1	Oral	Red Pharm Drug, Inc.	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Proficient Rx LP	2014-07-04	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2014-05-01	Not applicable	US
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Lupin Pharmaceuticals	2007-05-01	Not applicable	US
Cefdinir	Capsule	300 mg/1	Oral	Nu Care Pharmaceuticals,inc.	2008-01-07	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Cednir	Abbott
Cefdiel	Ranbaxy
Cefzon	Astellas
Duocef	Ranbaxy
Efdinir	Incepta
Idinir	Invision
Kefnir	Glenmark
Nirocef	Sel-J
Oceph	Zuventus
Omicef	Sel-J
Omnicef	Abbott Laboratories
Omnicef R	Janssen
Palacef	Renata
Palcef	Renata
Rtist	Lupin
Samnir	Siam Bheasach
Xi Fu Ni	Central Pharm
Zefdinir	Zydus
Zinir	FDC

Brand mixtures

Not Available

Categories

UNII

CI0FAO63WC

CAS number

91832-40-5

Weight

Average: 395.414
Monoisotopic: 395.035809931

Chemical Formula

C₁₄H₁₃N₅O₅S₂

InChI Key

RTXOFQZKPXMALH-GHXIOONMSA-N

InChI

InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

IUPAC Name

(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(C=C)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication

For the treatment of the respiratory, skin, soft tissue, and ENT infections caused by H. influenzae (including b-lactamase producing strains), H. parainfluenzae (including b-lactamase producing strains), S. pneumoniae (penicillin-susceptible strains), S. pyogenes, S. aureus (including b-lactamase producing strains), and M. catarrhalis.

Structured Indications

Pharmacodynamics

Cefdinir is a third generation cephalosporin with a broad spectrum of activity against enteric gram-negative rods. Cefdinir is stable in the presence of some, but not all, b-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins are susceptible to cefdinir. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal.

Mechanism of action

As with other cephalosporins, bactericidal activity of cefdinir results from inhibition of cell wall synthesis by acting on penicillin binding proteins (PBPs).

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Penicillin-binding protein 2	Protein	yes	inhibitor	Neisseria gonorrhoeae	P08149	details
PBP3	Protein	yes	inhibitor	Haemophilus influenzae	Q60FT7	details
Myeloperoxidase	Protein	no	inhibitor	Human	P05164	details

Absorption

Maximal plasma cefdinir concentrations occur 2 to 4 hours postdose following capsule or suspension administration. Estimated bioavailability of cefdinir capsules is 21% following administration of a 300 mg capsule dose, and 16% following administration of a 600 mg capsule dose. Estimated absolute bioavailability of cefdinir suspension is 25%. Absorption is reduced by approximately 15% when administered with a high fat meal.

Volume of distribution

0.35±0.29 L/kg [adult subjects]
0.67±0.38 L/kg [pediatric subjects (age 6 months to 12 years)]

Protein binding

60%-70%, binding is independent of concentration.

Metabolism

Cefdinir is not appreciably metabolized. Activity is primarily due to parent drug.

Route of elimination

Cefdinir is not appreciably metabolized. Cefdinir is eliminated principally via renal excretion with a mean plasma elimination half-life (t½) of 1.7 (±0.6) hours.

Half life

1.7 ± 0.6 hours

Clearance

renal cl=2 +/- 1 mL/min/kg [healthy]

Toxicity

Information on cefdinir overdosage in humans is not available. In acute rodent toxicity studies, a single oral 5600-mg/kg dose produced no adverse effects. Toxic signs and symptoms following overdosage with other b-lactam antibiotics have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Affected organisms

Enteric gram-negative rods

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
BCG vaccine	The therapeutic efficacy of Bcg can be decreased when used in combination with Cefdinir.	Investigational
Ferric Carboxymaltose	The serum concentration of Cefdinir can be decreased when it is combined with Ferric Carboxymaltose.	Approved
Ferric Citrate	The serum concentration of Cefdinir can be decreased when it is combined with Ferric Citrate.	Approved
Ferric pyrophosphate	The serum concentration of Cefdinir can be decreased when it is combined with Ferric pyrophosphate.	Approved
Iron	The serum concentration of Cefdinir can be decreased when it is combined with Iron.	Approved
Iron Dextran	The serum concentration of Cefdinir can be decreased when it is combined with Iron Dextran.	Approved, Vet Approved
Iron saccharate	The serum concentration of Cefdinir can be decreased when it is combined with Iron saccharate.	Approved
Picosulfuric acid	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefdinir.	Approved

Food Interactions

Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
Take without regard to meals.

References

Synthesis Reference

Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.

US6093814

General References

Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. [PubMed:1201739 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB14675
KEGG Drug	D00917
KEGG Compound	C08110
PubChem Compound	6915944
PubChem Substance	46505573
ChemSpider	5291705
ChEBI	3485
ChEMBL	CHEMBL927
Therapeutic Targets Database	DAP000436
PharmGKB	PA164768739
RxList	http://www.rxlist.com/cgi/generic2/cefdin.htm
Drugs.com	http://www.drugs.com/cdi/cefdinir.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/omn1519.shtml
Wikipedia	Cefdinir

ATC Codes

J01DD15 — Cefdinir

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (69.2 KB)

MSDS

Download (57 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Treatment	Osteomyelitis	1
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Treatment	Healthy Volunteers	4
2, 3	Completed	Treatment	Acute Otitis Media	1
4	Completed	Not Available	Healthy Volunteers	3
4	Completed	Treatment	Acute Bacterial Sinusitis (ABS)	2
4	Completed	Treatment	Acute Otitis Media	2
4	Completed	Treatment	Mild to Moderate Uncomplicated Skin and Skin Structure Infections	1
4	Recruiting	Treatment	Antibiotics / Pituitary Adenomas	1
4	Recruiting	Treatment	Pneumonia	1
Not Available	Completed	Treatment	Kwashiorkor / Marasmus	1
Not Available	Completed	Treatment	Snoring / Strep Throat	1

Pharmacoeconomics

Manufacturers

Aurobindo pharma ltd
Lupin ltd
Orchid healthcare
Sandoz inc
Teva pharmaceuticals usa
Abbott laboratories

Packagers

Abbott Laboratories Ltd.
A-S Medication Solutions LLC
Aurobindo Pharma Ltd.
Ceph International Corp.
DAVA Pharmaceuticals
Dispensing Solutions
Diversified Healthcare Services Inc.
Greenstone LLC
Lupin Pharmaceuticals Inc.
Murfreesboro Pharmaceutical Nursing Supply
Northstar Rx LLC
Orchid Healthcare
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Redpharm Drug
Resource Optimization and Innovation LLC
Sandoz
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.

Dosage forms

Form	Route	Strength
Capsule	Oral	300 mg/1
Powder, for suspension	Oral	125 mg/5mL
Powder, for suspension	Oral	250 mg/5mL

Prices

Unit description	Cost	Unit
Omnicef 125 mg/5ml Suspension 100ml Bottle	101.59USD	bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle	53.05USD	bottle
Omnicef 300 mg capsule	6.31USD	capsule
Omnicef 300 mg omni-pac capsule	5.72USD	capsule
Cefdinir 300 mg capsule	5.22USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US4935507	No	1994-12-04	2011-12-04	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	-0.2	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0878 mg/mL	ALOGPS
logP	0.02	ALOGPS
logP	-1.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.34 m³·mol^-1	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	-	0.7692
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.7205
P-glycoprotein substrate	Non-substrate	0.5185
P-glycoprotein inhibitor I	Non-inhibitor	0.9298
P-glycoprotein inhibitor II	Non-inhibitor	0.9165
Renal organic cation transporter	Non-inhibitor	0.8919
CYP450 2C9 substrate	Non-substrate	0.8676
CYP450 2D6 substrate	Non-substrate	0.8203
CYP450 3A4 substrate	Non-substrate	0.5821
CYP450 1A2 substrate	Non-inhibitor	0.7603
CYP450 2C9 inhibitor	Non-inhibitor	0.8303
CYP450 2D6 inhibitor	Non-inhibitor	0.894
CYP450 2C19 inhibitor	Non-inhibitor	0.8044
CYP450 3A4 inhibitor	Non-inhibitor	0.8436
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.953
Ames test	Non AMES toxic	0.6686
Carcinogenicity	Non-carcinogens	0.8339
Biodegradation	Not ready biodegradable	0.9925
Rat acute toxicity	1.8801 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9878
hERG inhibition (predictor II)	Non-inhibitor	0.8964

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-2983000000-72bf1ac3398fbaa1531b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Ketoximes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines

Substituents

Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Ketoxime / Tertiary carboxylic acid amide / Thiazole

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin, ketoxime (CHEBI:3485 )

Targets

Details

1. Penicillin-binding protein 2

Kind: Protein
Organism: Neisseria gonorrhoeae
Pharmacological action: yes
Actions: inhibitor

General Function:: Penicillin binding
Specific Function:: Synthesis of cross-linked peptidoglycan from the lipid intermediates.
Gene Name:: penA
Uniprot ID:: P08149
Uniprot Name:: Penicillin-binding protein 2
Molecular Weight:: 63649.54 Da

References

Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669 ]

Details

2. PBP3

Kind: Protein
Organism: Haemophilus influenzae
Pharmacological action: yes
Actions: inhibitor

General Function:: Penicillin binding
Specific Function:: Not Available
Gene Name:: pbp3
Uniprot ID:: Q60FT7
Uniprot Name:: PBP3
Molecular Weight:: 67295.025 Da

References

Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430 ]

Details

3. Myeloperoxidase

Kind: Protein
Organism: Human
Pharmacological action: no
Actions: inhibitor

General Function:: Peroxidase activity
Specific Function:: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:: MPO
Uniprot ID:: P05164
Uniprot Name:: Myeloperoxidase
Molecular Weight:: 83867.71 Da

References

Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056 ]

Transporters

Details

1. Solute carrier family 22 member 5

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Symporter activity
Specific Function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:: SLC22A5
Uniprot ID:: O76082
Uniprot Name:: Solute carrier family 22 member 5
Molecular Weight:: 62751.08 Da

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]

Details

2. Solute carrier family 15 member 1

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrateinhibitor

General Function:: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:: SLC15A1
Uniprot ID:: P46059
Uniprot Name:: Solute carrier family 15 member 1
Molecular Weight:: 78805.265 Da

References

Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]

Details

3. Solute carrier family 15 member 2

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Peptide:proton symporter activity
Specific Function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Uniprot Name:: Solute carrier family 15 member 2
Molecular Weight:: 81782.77 Da

References

Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:50

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Structure for DB00535 (Cefdinir)

Targets

References

References

References

Transporters

References

References

References